September 10, 2018

Ah, autumn- the season of cozy sweaters, hot drinks, and crisp walks through the leaf-strewn streets. Fall is fast approaching, and with it, the last chance for a getaway before the snow flies. And where better to go than New England, the picturesque home of the season?

Where are our sights set for this fall? Portland, Maine. It's the idyllic weekend escape, with one of the best food scenes in the country. Only a quick hop from New York or Boston, you can leave after work on a Friday and still be home for a solid 8 hour sleep before Monday hits.

48 hours in Portland Maine

Day 1

Arriving Friday evening, grab a cab and check into The Press Hotel. Located in what used to be a newspaper building, The Press Hotel is right in the centre of Old Port, an easy wander away from most of downtown.

After dropping off your things, make a beeline to Boda for Thai tapas and drinks- don’t miss the quail eggs! If you’re feeling lively, stop by The Jewel Box for a nightcap before turning in for the night.

Day 2

Waking up bright and early, go for a run through downtown to the Eastern Promenade to catch fantastic views of the Casco Bay Islands.  Make your way back the hotel via Bard Coffee for a pick-me-up before a quick shower. 

Freshly dressed, wander down Congress Street and stop at local favourite, Dutch’s, for brunch, before wandering towards Commercial Street. Make sure to check out Longfellow Books and Portland Dry Goods for some shopping, then head west to the Portland Museum of Art. If nothing else, admire their fantastic collection of Winslow Homer before catching a cab back uptown to Eventide Oyster co., where you can gorge yourself at one of the best raw bars on the East Coast.

From there, its a quick walk to the docks to catch your sunset cruise with Portland Schooner Sails, where you can enjoy a quiet sail around Casco Bay on a stunning century-old Maine schooner.

Sailboat on the Ocean

Once docked, head to Central Provisions for their daily menu. Put your name on the list and grab a drink downstairs to enjoy the buzzy atmosphere while you wait. Having eaten your fill, its a nice leisurely walk up Fore Street to Blue for their weekly Jazz night. When the music has wound down, the last stop of the day is the Portland Hunt & Alpine Club for some of the best cocktails in town.

Day 3

After a well-deserved lie-in, swing by Blake Orchard Juicery for a reviving smoothie bowl or juice before continuing to Cape Elizabeth.

If you’re in the mood for a relaxing day, bee-line to The Inn by the Sea and spend a couple hours in their spa. Otherwise, you can head out to Two Lights State Park for some instagram-worthy views and a beautiful walking trail. Either way, make sure to hit The Lobster Shack at Two Lights to find out why Maine Lobster is so famous. 

It’s time to head back in to town and grab your things. Time permitting, stop by Allagash Brewing Company for some of the best beer in Portland on your way to the airport. 


Did we miss any of your favourites in “the city by the sea”? Let us know in the comments below!

 In the mood for something more exotic? Check out our round-up of the 9 best luxury vacation rental properties here.

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